1,4-Dioxane → HCID 13732377, compound

HRID 648488

Reaction equation

HRID 648488 reaction equation
C1(O[C:8](=[O:30])[NH:9][C:10]2[CH:15]=[CH:14][C:13]([N:16]3[CH2:21][CH2:20][N:19]([C:22]4[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][CH:23]=4)[CH2:18][CH2:17]3)=[CH:12][CH:11]=2)C=CC=CC=1.C([N:33]([CH2:38][CH2:39][CH2:40][CH3:41])[CH2:34][C:35](O)=[O:36])C.O1CCOCC1>CN(C)C1C=CN=CC=1.O>[CH2:38]([N:33]1[CH2:34][C:35](=[O:36])[N:9]([C:10]2[CH:15]=[CH:14][C:13]([N:16]3[CH2:17][CH2:18][N:19]([C:22]4[CH:23]=[CH:24][C:25]([O:28][CH3:29])=[CH:26][CH:27]=4)[CH2:20][CH2:21]3)=[CH:12][CH:11]=2)[C:8]1=[O:30])[CH2:39][CH2:40][CH3:41]

Participants

6

Reactant 3

HCID 312751,4-DioxaneHCID 981607Phenyl N-(4-(4-(4-methoxyphenyl)piperazin-1-yl)phenyl)carbamateHCID 22062329HCID 22062329, compound

Product 1

HCID 13732377HCID 13732377, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 962WaterSolvent

Procedure

A mixture of 24 parts of phenyl[4-[4-(4-methoxyphenyl)-1-piperazinyl]phenyl]carbamate, 15.9 parts of ethyl N-butylglycine, 2 parts of N,N-dimethyl-4-pyridinamine and 200 parts of 1,4-dioxane was stirred and refluxed overnight. Then water was added and stirring was continued for a while. The reaction mixture was cooled, poured onto water and the whole was stirred. The precipitated product was filtered off, washed with water and dissolved in 150 parts of trichloromethane. This solution was stirred for 30 minutes with 3 parts of silica gel. The latter was filtered off and the filtrate was evaporated. The residue was crystallized from butanol. The product was filtered off and dried in vacuo at 60° C., yielding 2.3 parts of 1-butyl-3-[4-[4-(4-methoxyphenyl)-1-piperazinyl]phenyl]-2,4-imidazolidinedione; mp. 183.7° C. (39).

Workup

  1. temperaturerefluxed overnight
  2. stirringstirring
  3. temperatureThe reaction mixture was cooled
  4. additionpoured onto water
  5. stirringthe whole was stirred
  6. filtrationThe precipitated product was filtered off
  7. washwashed with water
  8. dissolutiondissolved in 150 parts of trichloromethane
  9. stirringThis solution was stirred for 30 minutes with 3 parts of silica gel
  10. filtrationThe latter was filtered off
  11. customthe filtrate was evaporated
  12. customThe residue was crystallized from butanol
  13. filtrationThe product was filtered off
  14. customdried in vacuo at 60° C.

Sources & evidence

ORD record
ord-a58dcbe881a44734a4c7308289c6ecda
Source dataset
uspto-grants-1988_04
Patent number
US04735942

Linked notes

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